Quantum Computational, Spectroscopic, Hirshfeld Surface Analysis of 3-Picoline (Monomer and Dimer) by DFT/TD-DFT with Different Solvents, Molecular Docking, and Molecular Dynamic Studies

References

• G. K. Sims, and L. E. Sommers, “Biodegradation of Pyridine Derivatives in Soil Suspensions,” Environmental Toxicology and Chemistry 5, no. 6 (1986): 503–9.
   Web of Science ®Google Scholar
• R. L. Frank, and R. P. Seven, “Pyridines. IV. A Study of the Chichibabin Synthesis,” Journal of the American Chemical Society 71, no. 8 (1949): 2629–35.
   Web of Science ®Google Scholar
• B. Elvers, Ullmann's encyclopedia of industrial chemistry, Vol. 17 (Hoboken, NJ: Verlag Chemie, 1991), p. 363–376.
   Google Scholar
• C. Ley, B. Elvers, G. Bellussi, J. Bus, K. Drauz, H. Greim, V. Hessel, A. Kleemann, B. Kutscher, G. Meijer and S. Moran, Ullmann’s encyclopedia of industrial chemistry (Chichester, UK: Wiley, 2010).
   Google Scholar
• I. López Tocón, M. S. Woolley, J. C. Otero, and J. I. Marcos, “Vibrational Spectrum of 3-Methyl and 4-Methylpyridine,” Journal of Molecular Structure 470, no. 3 (1998): 241–6.
   Web of Science ®Google Scholar
• T. G. Gulyamova, A. M. Kerbalaeva, K. V. Lobanova, N. Zh Sagdiev, and E. S. Sadykov, “Transformation of 3-Methylpyridine into Nicotinic Acid by the Yeast S. cerevisiae,” Chemistry of Natural Compounds 42, no. 2 (2006): 212–5.
   Web of Science ®Google Scholar
• G. K. Sims, E. J. O’Loughlin, and R. L. Crawford, “Degradation of Pyridines in the Environment,” Critical Reviews in Environmental Control 19, no. 4 (1989): 309–40.
   Web of Science ®Google Scholar
• G. K. Sims, and L. E. Sommers, “Degradation of Pyridine Derivatives in Soil,” Journal of Environmental Quality 14, no. 4 (1985): 580–4.
   Web of Science ®Google Scholar
• (a) N. Siddiqui, and S. Javed, “Quantum Computational, Spectroscopic Investigations on Ampyra (4-Aminopyridine) by Dft/Td-Dft with Different Solvents and Molecular Docking Studies,” Journal of Molecular Structure 1224 (2021): 129021.
   Web of Science ®Google Scholar
  (b) A. Fatima, J. Bhadoria, S. K. Srivastava, I. Verma, N. Siddiqui, and S. Javed, “Exploration of Experimental and Theoretical Properties of 5, 5-Dimethyl 3-Amino-Cyclohex-2-en-1-One (AMINE DIMEDONE) by DFT/TD-DFT with Ethanol and DMSO as Solvents and Molecular Docking Studies,” Journal of Molecular Liquids 338 (2021): 116551.
   Web of Science ®Google Scholar
  (c) A. Fatima, K. Pooja, S. Savita, M. Singh, I. Verma, N. Siddiqui, and S. Javed, “Quantum Chemical, Experimental Spectroscopic, Hirshfeld Surface and Molecular Docking Studies of the anti-Microbial Drug Sulfathiazole,” Journal of Molecular Structure 1245 (2021): 131118.
   Web of Science ®Google Scholar
  (d) A. Fatima, G. Khanum, S. Savita, K. Pooja, I. Verma, N. Siddiqui, and S. Javed, “Quantum Computational, Spectroscopic, Hirshfeld Surface, Electronic State and Molecular Docking Studies on Sulfanilic Acid: An anti-Bacterial Drug,” Journal of Molecular Liquids 346 (2022): 117150.
   Web of Science ®Google Scholar
  (e) A. Fatima, G. Khanum, A. Sharma, K. Garima, S. Savita, I. Verma, N. Siddiqui, and S. Javed, “Computational, Spectroscopic, Hirshfeld Surface, Electronic State and Molecular Docking Studies on Phthalic Anhydride,” Journal of Molecular Structure 1249 (2022): 131571.
   Web of Science ®Google Scholar
  (f) A. Fatima, G. Khanum, S. K. Srivastava, I. Verma, N. Siddiqui, and S. Javed, “Synthesis, Computational, Spectroscopic, Hirshfeld Surface, Electronic State and Molecular Docking Studies on Diethyl-5-Amino-3-Methylthiophene-2, 4-Dicarboxylate,” Chemical Physics Letters 784 (2021): 139103.
   Web of Science ®Google Scholar
  (g) A. Fatima, G. Khanum, A. Sharma, I. Verma, H. Arora, N. Siddiqui, and S. Javed, “Experimental Spectroscopic, Computational, Hirshfeld Surface, Molecular Docking Investigations on 1H-Indole-3-Carbaldehyde,” Polycyclic Aromatic Compounds (2022): 1–25.
   Web of Science ®Google Scholar
  (h) A. Fatima, M. Singh, N. Agarwal, I. Verma, R. J. Butcher, N. Siddiqui, and S. Javed, “Spectroscopic, Molecular Structure, Electronic, Hirshfeld Surface, Molecular Docking, and Thermodynamic Investigations of Trans-4-hydroxy-L-Proline by DFT Method,” Journal of Molecular Liquids 343 (2021): 117549.
   Web of Science ®Google Scholar
  (i) A. Fatima, M. Singh, N. Singh, S. Savita, I. Verma, N. Siddiqui, and S. Javed, “Investigations on Experimental, Theoretical Spectroscopic, Electronic Excitations, Molecular Docking of Sulfaguanidine (SG): An Antibiotic Drug,” Chemical Physics Letters 783 (2021): 139049.
   Web of Science ®Google Scholar
• N. Dege, H. Gökce, O. E. Doğan, G. Alpaslan, T. Ağar, S. Muthu, and Y. Sert, “Quantum Computational, Spectroscopic Investigations on N-(2-((2-Chloro-4, 5-Dicyanophenyl) Amino) Ethyl)-4-Methylbenzenesulfonamide by DFT/TD-DFT with Different Solvents, Molecular Docking and Drug-Likeness Researches,” Colloids and Surfaces A: Physicochemical and Engineering Aspects 638 (2022): 128311.
   Web of Science ®Google Scholar
• A. A. Abdulridha, M. A. A. H. Allah, S. Q. Makki, Y. Sert, H. E. Salman, and A. A. Balakit, “Corrosion Inhibition of Carbon Steel in 1 M H2SO4 Using New Azo Schiff Compound: Electrochemical, Gravimetric, Adsorption, Surface and DFT Studies,” Journal of Molecular Liquids 315 (2020): 113690.
   Web of Science ®Google Scholar
• M. Gümüş, ŞN. Babacan, Y. Demir, Y. Sert, İ. Koca, and İ. Gülçin, “Discovery of Sulfadrug–Pyrrole Conjugates as Carbonic Anhydrase and Acetylcholinesterase Inhibitors,” Archiv Der Pharmazie 355, no. 1 (2022): 2100242.
   PubMed Web of Science ®Google Scholar
• A. A. Balakit, S. Q. Makki, Y. Sert, F. Ucun, M. B. Alshammari, P. Thordarson, and G. A. El-Hiti, “Synthesis, Spectrophotometric and DFT Studies of New Triazole Schiff Bases as Selective Naked-Eye Sensors for Acetate Anion,” Supramolecular Chemistry 32, no. 10 (2020): 519–26.
   Web of Science ®Google Scholar
• G. Raja, G. Venkatesh, J. S. Al-Otaibi, P. Vennila, Y. S. Mary, and Y. Sixto-López, “Synthesis, Characterization, Molecular Docking and Molecular Dynamics Simulations of Benzamide Derivatives as Potential anti-Ovarian Cancer Agents,” Journal of Molecular Structure 1269 (2022): 133785.
   Web of Science ®Google Scholar
• G. Venkatesh, Y. Sixto-López, P. Vennila, Y. S. Mary, J. Correa-Basurto, Y. S. Mary, and A. Manikandan, “An Investigation on the Molecular Structure, Interaction with Metal Clusters, anti-Covid-19 Ability of 2-deoxy-D-Glucose: DFT Calculations, MD and Docking Simulations,” Journal of Molecular Structure 1258 (2022): 132678.
   Web of Science ®Google Scholar
• G. Venkatesh, Y. Sheena Mary, Y. Shymamary, V. Palanisamy, and M. Govindaraju, “Quantum Chemical and Molecular Docking Studies of Some Phenothiazine Derivatives,” Journal of Applied Organometallic Chemistry 1, no. 3 (2021): 148–58.
   Google Scholar
• G. Venkatesh, C. Kamal, P. Vennila, M. Govindaraju, Y. S. Mary, S. Armakovic, S. J. Armakovic, S. Kaya, and C. Y. Panicker, “Molecular Dynamic Simulations, ALIE Surface, Fukui Functions Geometrical, Molecular Docking and Vibrational Spectra Studies of Tetra Chloro p and m-Xylene,” Journal of Molecular Structure 1171 (2018): 253–67.
   Web of Science ®Google Scholar
• J. E. Davies, “3-Picoline,” ActaCrystallographica Structure Report Online E57 (2001): 01087–8.
   Google Scholar
• M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, R. Cheeseman, J. Montgomer, T. Vreven, K. N. Kudin, J. C. Burant, et al, Gaussian 03, Revision C. 02 (Wallingford, CT: Gaussian Inc., 2004).
   Google Scholar
• F. Neese, “The ORCA Program System, Wiley Interdiscip,” WIREs Computational Molecular Science 2, no. 1 (2012): 73–8.
   Google Scholar
• M. H. Jomroz, Vibrational Energy Distribution Analysis, VEDA4 (Warsaw, Poland: Institute of Nuclear Chemistry and Technology, 2004).
   Google Scholar
• T. Lu, and F. Chen, “Multiwfn: A Multifunctional Wavefunction Analyzer,” Journal of Computational Chemistry 33, no. 5 (2012): 580–92.
   PubMed Web of Science ®Google Scholar
• Origin 8.0, OriginLab Corp. (Northampton, MA).
   Google Scholar
• A. Daina, O. Michielin, and V. Zoete, Sci Rep 7, 42717. 24-R. Dennington, T. Keith, J. Millam, GaussView, version 4.12 Semichem (Merriam, Kansas: Shawnee Mission, K.S. Inc., 2017).
   Google Scholar
• F. L. Hirshfeld, “Bonded-Atom Fragments for Describing Molecular Charge Densities,” Theoretica Chimica Acta 44, no. 2 (1977): 129–38.
   Google Scholar
• M. A. Spackman, and D. Jayatilaka, “Hirshfeld Surface Analysis,” CrystEngComm 11, no. 1 (2009): 19–32.
   Web of Science ®Google Scholar
• W. Wang, Y. Ling, L.-J. Yang, Q.-L. Liu, Y.-H. Luo, and B.-W. Sun, “Crystals of 4-(2- Benzimidazole)-1,2,4-Triazole and Its Hydrate: Preparations, Crystal Structure and Hirshfeld Surfaces Analysis,” Research on Chemical Intermediates 42, no. 4 (2016): 3157–68.
   Web of Science ®Google Scholar
• T. C. Lu, and F.-W. Chen, “Calculation of Molecular Orbital Composition,” ActaChim Sinica 69 (2011): 2393–406.
   Web of Science ®Google Scholar
• D. Sajan, I. H. Joe, and V. S. Jayakumar, “NIR-FT Raman, FT-IR and Surface-Enhanced Raman Scattering Spectra of Organic Nonlinear Optic Material: p-Hydroxyacetophenone,” Journal of Raman Spectroscopy 37, no. 4 (2006): 508–19.
   Web of Science ®Google Scholar
• M. Gussoni, C. Castiglioni, M. N. Ramos, M. C. Rui, and G. Zerbi, “Infrared Intensities: From Intensity Paparmeters to an Overall Understanding of the Spectrum,” Journal of Molecular Structure. 224 (1990): 445–70.
   Web of Science ®Google Scholar
• R. Ditchfield, “Molecular Orbital Theory of Magnetic Aheilding and Magnetic Susceptibility,” The Journal of Chemical Physics 56, no. 11 (1972): 5688–91.
   Web of Science ®Google Scholar
• R. Lu, W. Gan, B. Wu, Z. Zhang, Y. Guo, and H. Wang, “C-H Stretching Vibrations of Methyl, Methylene and Methine Groups at the Vapor/Alcohol (N = 1-8) Interfaces,” The Journal of Physical Chemistry B 109, no. 29 (2005): 14118–29.
   PubMed Web of Science ®Google Scholar
• J. S. Murray, J. M. Seminario, M. C. Concha, and P. Politzer, “An Analysis of Molecular Electrostatic Potentials Obtained by a Local Density Functional Approach,” International Journal of Quantum Chemistry 44, no. 2 (1992): 113–22.
   Web of Science ®Google Scholar
• J. Poater, M. Duran, M. Sol, and B. Silvi, “Theoretical Evaluation of Electron delocalization in aromatic Molecules by Means of Atoms in Molecules (AIM) and Electron Localization Function (ELF) Topological Approaches,” Chemical Reviews 105, no. 10 (2005): 3911–47.
   PubMed Web of Science ®Google Scholar
• J. Henriksson, T. Saue, and P. Norman, “Quadratic Response Functions in the Relativistic Four Component Kohn- Sham Approximation,” The Journal of Chemical Physics 128, no. 2 (2008): 024105.
   PubMed Web of Science ®Google Scholar
• C. Cassidy, J. M. Halbout, W. Donaldson, and C. L. Tang, “Nonlinear Optical Properties of Urea,” Optics Communications 29, no. 2 (1979): 243–6.
   Web of Science ®Google Scholar
• C. S. Abraham, J. C. Prasana, and S. Muthu, “Quantum Mechanical, Spectroscopic and Docking Studies of 2-Amino-3-Bromo-5-Nitropyridine by Density Functional Method,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 181 (2017): 153–63.
   PubMed Web of Science ®Google Scholar
• K. Fukui, “Role of Frontier Orbitals in Chemical Reactions,” Science (New York, NY) 218, no. 4574 (1982): 747–54.
   Google Scholar
• S. Balachandar, M. Dhandapani, Biological action of molecular adduct pyrazole: trichloroacetic acid on candida albicans and ctDNA-A combined experimental, Fukui functions calculation and molecular docking analysis. Journal of Molecular Structure 1184 (2019): 129–138.
   Google Scholar
• A. Shalini, H. Tandon, and T. Chakraborty, Journal of Bioequivalence and Bioavailability 09 (2017): 518–27.
   Google Scholar
• B. Ruscic, J. E. Boggs, A. Burcat, A. G. Csaszar, J. Demaison, R. Janoshek, J. M. L. Martin, and M. L. Morton, "IUPAC critical evaluation of thermochemical properties of selected radicals," American Institute of Physics 34 (2005): 573–656.
   Google Scholar
• D. A. Safin, K. Robeyns, and Y. Garcia, “1,2,4-Triazole-Based Molecular Switches: Crystal Structures, Hirshfeld Surface Analysis and Optical Properties,” CrystEngComm 18, no. 38 (2016): 7284–96.
   Web of Science ®Google Scholar
• D. R. Roy, R. Parthasarathi, B. Maiti, V. Subramanian, and P. K. Chattaraj, “Electrophilicity Index as a Possible Descriptor for Toxicity Prediction,” Bioorganic & Medicinal Chemistry 13, no. 10 (2005): 3405–12.
   PubMed Web of Science ®Google Scholar
• E. F. Pettersen, T. D. Goddard, C. C. Huang, G. S. Couch, D. M. Greenblatt, E. C. Meng, and T. E. Ferrin, “USCF -A Visualization System for Exploratory Resaecrh and Analysis,” Journal of Computational Chemistry 25, no. 13 (2004): 1605–12.
   PubMed Web of Science ®Google Scholar
• P. Singh, P. Sharma, K. Bisetty, and J. J. Perez, “Molecular Dynamics Simulations of Ac-3Aib-Cage-3Aib-NHMe,” Molecular Simulation 36, no. 13 (2010): 1035–44.
   Web of Science ®Google Scholar
• D. M. van Aalten, R. Bywater, J. B. Findlay, M. Hendlich, R. W. Hooft, and G. Vriend, “PRODRG, a Program for Generating Molecular Topologies and Unique Molecular Descriptors from Coordinates of Small Molecules,” Journal of Computer-Aided Molecular Design 10, no. 3 (1996): 255–62.
   PubMed Web of Science ®Google Scholar
• C. A. Lipinski, F. Lombardo, B. W. Dominy, and P. J. Feeney, “Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings,” Advanced Drug Delivery Reviews 46, no. 1–3 (2001): 3–26.
   PubMed Web of Science ®Google Scholar
• A. Daina, O. Michielin, and V. Zoete, “SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules,” Scientific Reports (2017): 1–13.
   PubMedGoogle Scholar